If you ever need guidance on funding options for flips or rentals, I’d be happy to help.

What I recall from Aaron's deals was it wasn't about finding ever larger seller financed deals, but keeping the old seller as essentially a PML....keeping you from constantly looking for new funding when you already have someone that agreed to fund you essentially. 

Most hosts in Chicago just pocket the full funds from direct booking, you would be in the very very small majority if actually paid city taxes on it.

How you funding it?

Quote from @Micheal Smoke: Hi, my name is Mike Smoke, and I'm an aspiring real estate investor focusing on multifamily and Section 8 properties in the U.S. as the barrier to entry is much much lower in terms of price compared to Canada and Funding options. 

Try COGO funding, as this is their funding...go straight to them maybe?

You're likely best off wholesaling the property and using those funds to invest in the deal or invest in something else.

I have been investing mainly in trust deeds but like you got connected with Dave and just recently ended up investing in his fund, my primary reason was for diversification and because it is passive. 

Example; I am invested in a fund that does active option plays on Tesla.

Equity Created: $550,000 ARV - $409,000 loan balance = $141,000 in equity.Cash Flow: The property rents for $2,950/month, covering all expenses and generating slight positive cash flow.HELOC Potential: Post-refi, I can secure a HELOC up to $86,000 (90% LTV) to fund future investments.